165683-01-2

Basic information

• Product Name: 2-Phenylamino-thiazole-4-carboxylic acid
• Synonyms: 2-Anilino-1,3-thiazole-4-carboxylic acid, 4-Carboxy-2-(phenylamino)-1,3-thiazole;2-(phenylamino)-4-thiazolecarboxylic acid
• CAS NO: 165683-01-2
• Molecular Formula: C₁₀H₈N₂O₂S
• Molecular Weight: 220.25
• Product Categories: pharmacetical
• Mol File: 165683-01-2.mol

Chemical Properties

• Melting Point: 278-280°C
• Boiling Point: 435°Cat760mmHg
• Flash Point: 216.9°C
• Appearance: /
• Density: 1.461g/cm³
• Storage Temp.: 2-8°C
• PKA: 1.10±0.10(Predicted)
• CAS DataBase Reference: 2-Phenylamino-thiazole-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylamino-thiazole-4-carboxylic acid(165683-01-2)
• EPA Substance Registry System: 2-Phenylamino-thiazole-4-carboxylic acid(165683-01-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 165683-01-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
2-Phenylamino-thiazole-4-carboxylic acid is used as a key intermediate in the synthesis of pharmaceuticals for its potential to exhibit a variety of biological activities. Its structural features allow for the development of drugs that can target specific enzymes or pathways involved in disease processes.
Used in Antimicrobial Applications:
In the field of antimicrobials, 2-Phenylamino-thiazole-4-carboxylic acid is utilized as an active ingredient for its ability to combat microbial infections. Its antimicrobial properties make it a candidate for the development of new antibiotics or antifungal agents to address the growing issue of drug-resistant pathogens.
Used in Anti-fungal Applications:
Similarly, in antifungal applications, 2-Phenylamino-thiazole-4-carboxylic acid serves as a potential therapeutic agent to treat fungal infections. Its antifungal properties can be harnessed to develop new treatments for a variety of fungal diseases.
Used in Enzyme Inhibition:
2-Phenylamino-thiazole-4-carboxylic acid is used as an enzyme inhibitor in the development of drugs targeting specific enzymes. Its capacity to inhibit certain enzymes can be crucial in treating diseases where enzyme dysregulation plays a significant role.
Used in Drug Discovery Research:
In the research industry, 2-Phenylamino-thiazole-4-carboxylic acid is used as a starting material or a scaffold in drug discovery. Its unique structure provides a foundation for the design and synthesis of new compounds with potential therapeutic effects.
Further research is necessary to fully explore and exploit the potential applications of 2-Phenylamino-thiazole-4-carboxylic acid in the pharmaceutical and medical fields, ensuring its development into effective and safe treatments.

Upstream product

• 103-85-5 monophenylthiourea 
• 126533-76-4 ethyl 2-(N-phenylamino)thiazole-4-carboxylate 

Downstream Products

• 1023652-35-8 C₂₀H₂₁N₅OS 
• 1311195-85-3 (2-(phenylamino)thiazol-4-yl)(3,4,5-trimethoxyphenyl)methanone 
• 1311195-91-1 (2-(phenylamino)thiazol-4-yl)(3,4,5-trimethoxyphenyl)methanone hydrochloride 
• 1311196-06-1 N-methoxy-N-methyl-2-(phenylamino)thiazole-4-carboxamide 

Relevant articles and documents

Design, synthesis, and SAR studies of 4-substituted methoxylbenzoyl-aryl- thiazoles analogues as potent and orally bioavailable anticancer agents

In a continued effort to improve upon the previously published 4-substituted methoxybenzoyl-aryl-thiazole (SMART) template, we explored chemodiverse "B" rings and "B" to "C" ring linkage. Further, to overcome the poor aqueous solubility of this series of agents, we introduced polar and ionizable hydrophilic groups to obtain water-soluble compounds. For instance, based on in vivo pharmacokinetic (PK) studies, an orally bioavailable phenyl-amino-thiazole (PAT) template was designed and synthesized in which an amino linkage was inserted between "A" and "B" rings of compound 1. The PAT template maintained nanomolar (nM) range potency against cancer cell lines via inhibiting tubulin polymerization and was not susceptible to P-glycoprotein mediated multidrug resistance in vitro, and markedly improved solubility and bioavailability compared with the SMART template (45a-c (PAT) vs 1 (SMART)).

COMPOUNDS FOR TREATMENT OF CANCER

The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.

Discovery of 2-aminothiazole-4-carboxamides, a novel class of muscarinic M3 selective antagonists, through solution-phase parallel synthesis

Synthesis and structure-activity relationship of a new class of muscarinic M3 selective antagonists were described. In the course of searching for a muscarinic M3 antagonist with a structure distinct from those of the 2-(4,4-difluorocyclopentyl)-2-phenylacetamide derivatives, we identified a thiazole-4-carboxamide derivative (1) as a lead compound in our in-house chemical collection. Since this compound (1) showed relatively low binding affinity (K1 = 140 nM) for M3 receptors in the human binding assays, we tried to improve its potency and selectivity for M 3 over M1 and M2 receptors by derivatization of 1 through a combinatorial approach. A solution-phase parallel synthesis effectively contributed to the optimization of each segment of 1. Thus, we have identified a cyclooctenylmethyl derivative (3e) and a cyclononenylmethyl derivative (3f) as representative M3 selective antagonists in this class.